Sleepy Hollow

“A drowsy, dreamy influence seems to hang over the land, and to pervade the very atmosphere.”

So Washington Irving describes Sleepy Hollow in his famous story, The Legend of Sleepy Hollow. Historically the town has been renowned for its ghosts and haunting aura. Now, it’s known for its many Halloween traditions, with people coming from all over the state to celebrate the holiday.

Every year since I moved to the city, I’ve wanted to visit Sleepy Hollow. But in past years I wouldn’t remember until mid October, and by then all of the activities were sold out. So this year, I made a calendar reminder in August to start planning. And I’m glad I did! When tickets went on sale September 1st, I was ready to buy them for everything that we planned to fit into one very festive day and night:

Lyndhurst: Historic Tours with a Halloween Twist

Evening Lantern Tour of the Sleepy Hollow Cemetery

Horseman’s Hollow

Great Jack O’Lantern Blaze

Ann, Jess, Steph and I were lucky enough to visit Sleepy Hollow on one of the only beautiful weekends in October. We arrived around lunchtime, and headed to the Bridge View Tavern for a bite to eat. Although the views weren’t quite as picturesque as you would imagine from the name, the food was good, especially the fries!

While we were walking in, we noticed that the town had festive orange street signs rather than the standard green ones. How cute is that?!

We then drove over to Lyndhurst, a gorgeous Gothic Revival mansion in the Hudson Valley.

There were scarecrows covering the fields of the entrance, decorated by local organizations and students.

One looked particularly familiar.

Lyndhurst itself is gorgeous, and it’s easy to see why the mansion has been featured in so many movies and TV shows.

Clearly the mansion was getting into the Halloween spirit!

Get it? Spirit?!

We did a tour of the mansion which was really interesting. The guide asked us our names, and incorporated us into the stories that he told, which I thought was pretty fun.

Like the outside, the inside of the mansion was decorated for Halloween. In some rooms there were so many decorations that I thought that it took away from the beauty of the home. However I did like how the dining room was decorated. That is a dinner party I would not like to attend!

The guide also asked questions, and quizzed us on New York trivia related to the mansion. I did well… since another man on the tour kept giving me the answers!

Afterwards we wandered around the grounds of the estate and enjoyed the beautiful autumn weather.

We found an old well, and when we looked inside we could only see the branches of whatever was growing inside. Curious to see how deep the well was, we found the biggest rock we could and dropped it into the hole. We waited with baited breath to see just how long it would fall… only to have it thud to the earth at ground level. We laughed so hard, not expecting the well to have been filled in. So much for that experiment!

We then drove back into Sleepy Hollow to explore the town a little bit. I was picturing a cute little town decorated for the holiday, like the real-life version of Stars Hollow from Gilmore Girls. So we were disappointed to find out that the town wasn’t all that cute, and didn’t have that many dining options.

But it did have orange firetrucks, so that’s pretty fun!

After meeting some of the firemen who drive the orange trucks, and grabbing a quick slice of pizza, we headed off to our evening adventures… aka the spooky Halloween activities that make Sleepy Hollow famous.

When I began planning the visit in August, the cemetery’s website hadn’t been updated to indicate what time the October tours would be offered. So I called the cemetery to ask (I was serious about this planning!) and left a message. I completely forgot about the call, and then a few days later I received a voicemail from an unknown number. I pressed play, and heard “Hi Ashley, this is Christine from the cemetery…” You can imagine how confused I was until I finally remembered my earlier message!

The night we were there there was almost a full moon, so the ambiance was perfect.

As we walked, the guide told us the legend that inspired Washington Irving’s story. During the Revolutionary War, a German solider who rode on horseback was decapitated by a canon during a nearby battle. The man was buried by the Van Tassel family in an unmarked grave in the Old Dutch Burying Ground in what is now Sleepy Hollow Cemetery. Local legend has it that the man rises up from his grave every Halloween, desperately seeking his lost head.

Sleepy Hollow Cemetery is sprawling, with old, historic gravestones mingled with giant mausoleums ten times the size of my New York apartment! I thought that the tour was done in very good taste, and was respectful of the people interred on the grounds without trying to be scary or creepy. We learned a lot about the history of Sleepy Hollow, and that many famous people are buried there including Andrew Carnegie, Walter Chrysler, Elizabeth Arden, dozens of Astors and Rockefellers, and fittingly, Washington Irving.

One of my favorite parts of the tour was when the guide pointed out the grave of Francis Pharcellus Church, the editor of the New York Sun who penned Yes, Virginia, there is a Santa Claus. I love that message!

After our cemetery tour, we moved on to Horseman’s Hollow, an outdoor haunted house on the grounds of Sleepy Hollow’s historic Philipsburg Manor. There are a variety of creepy buildings as you walk along the trail, and terrifying figures jump out at you from all angles.

It was fun to do, and very classic Halloween, but it wasn’t scary. The times that we screamed were when things jumped out and surprised us, and this was more for fun than because we were scared. Even Steph, who had been dreading the haunted trail (for a full month and a half!) had a good time and didn’t think that it was scary.

And at the end of Horseman’s Hollow was the horseman himself. Guess he hasn’t found his head yet!

To end our night, we headed just outside of Sleepy Hollow to the Great Jack O’Lantern Blaze, which is set along the mysterious backdrop of Van Cortlandt Manor’s 18th-century buildings.

It was so amazing, and one of our favorite parts of the trip!

The Blaze has trails with over 10,000 hand-carved pumpkins arranged in the most unique ways. Each night, it takes 30 volunteers 3 hours to light all of the candles inside the pumpkins!

This train is formed entirely out of carved pumpkins! How amazing is that?!

So is this dragon!

The very top of this pumpkin says, “Will you Marry Me?” Isn’t that cute?

Ann said no…

We all loved the Great Jack O’Lantern Blaze! It’s not to be missed!

A LOT went into planning this visit! We had four things that we wanted to do, and only had one day and night to do them. So I spent a lot of time figuring out when it was best to do what (visitsleepyhollow.com is a lifesaver!). I even checked what time sunset was to make sure we didn’t do any of the evening activities too early!

The number one thing to know? DEFINITELY book your tickets when they’re made available on September 1st! Sleepy Hollow tickets sell out quickly, and if you’re trying to do multiple things in one night you want to make sure that you have your desired ticket time slots.

You’ll also want to have your own car. While you can take the train and then use taxis, if you’re doing several activities in one night then calling and waiting for a taxi would take too much time, and you’ll have more freedom if you drive.

This is what else I recommend as far as timing, and everything that you need to know to make the experience better:

Lyndhurst: Historic Tours with a Halloween Twist

Location: 635 South Broadway, Tarrytown, NY

Cost: $18

Ideal time: Afternoon. This is a great place to visit while it’s light out, since the grounds and the trees are gorgeously colorful in the fall.

Length: The tours are an hour, and then you’ll want to spend some time exploring the grounds on your own.

Cost: $25 or $40 for fast track tickets (Saturday prices). DEFINIELY get the fast track tickets. The line for those without fast passes is incredibly long, and if you have a lot that you’re trying to get done in one night (like we were) why waste time in line? Plus the cost isn’t that much more, and as us New Yorkers know time is money!

Ideal time: 9pm

Length: Once you start the trail, you should get through it in about 30 minutes. However there are lines getting into the trail, and those will be much shorter if you have fast track tickets!

What to know: You can park for free beginning 30 minutes before your ticket time. If you’re looking for bathrooms while you’re at Horseman’s Hollow, there are real ones inside the store.

Hack: Get the fast track ticket for the time before you want to go, so you can walk right in when you arrive. We had fast passes for 9pm, and our lantern tour was done at 9pm. Including the time it took to leave the cemetery, park at the Horseman’s Hollow, and walk over to the line, we got there at about 9:30pm. However, since we had 9pm fast passes, I convinced them to let us go in front of the people who had 9:30pm fast passes. So not only did we get in front of people with normal tickets, but we also got in front of everyone else with fast track tickets.

Ideal time: 10:30pm. We were back on schedule when we arrived at the Great Jack O’Lantern Blaze. It closes at 11:30pm, and we finished at 11:22pm. Nailed it. Plus, since 10:30pm is the latest time slot available, it wasn’t as crowded as it would be earlier in the night, when most of the families go.

Length: You’ll walk through it in about 45 minutes to an hour, depending on how many times you stop to take pictures!

What to know: The Blaze is a 20-minute drive outside of Sleepy Hollow (where the Cemetery and Horseman’s Hollow are located). So you don’t want to schedule the Blaze in the middle of your activities, because you’ll waste too much time driving from Sleepy Hollow to the Blaze and then back to Sleepy Hollow. And you can park for free 30 minutes before your scheduled ticket time.

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Just wanted to let you know incase you plan on coming back that there is actually a cute “Stars Hollow”-type town, but it’s actually the main street of Tarrytown. Sleepy Hollow and Tarrytown used to all be one town so its actually very close even though it has another name. You wanted Main Street in Tarrytown. Theres tons of dining there! Beeckman Ave. (where you guys were) doesn’t have much worth a visit. Hope you will come back and enjoy the fall events and the actual town! It’s worth a trip back!